Ralph Lauren quietly shuttered its two-year-old 20,000-square-foot store last week. Other brands are expected to close boutiques in a city that has lost its luster for cash-rich mainland Chinese tourists.

A Mighty Plan

A new breeze blows through Chicago.

These days, dismissing Chicago as simply one of the fly-over states is passé. Nor is it any longer, as poet Carl Sandburg phrased it, “hogbutcher to the world.” In fact, the Windy City is now being touted for its burgeoning restaurant scene, fashion-forward boutiques and standout architecture.

Of course, it didn’t hurt when Vince Vaughn squired his then-love Jennifer Aniston around town (even throwing out a pitch at a Cubs game while Aniston watched in the stands), and that stars like Brad and Angelina have been snapped by paparazzi cruising Lake Michigan with their brood in tow. And, yes, there’s Oprah. Regardless of the celebrity appeal, Chicago is proving that it is a city, indeed, to again quote Sandberg, of “big shoulders.”

The city rebuilt itself once after the Great Fire in 1871, and it’s undergoing the same kind of rebirth today. In 2004, construction was completed on Millennium Park, a $500 million public space that features an impressive collection of postmodern architecture, including the Frank Gehry–designed Jay Pritzker Pavilion. A year later, the defunct rock concert Lollapalooza began again—moving to its now-permanent home in downtown’s Grant Park. Then last year, the Chicago History Museum underwent a major overhaul—renovating three-quarters of the building and adding a restaurant, overseen by Wolfgang Puck. And in the spring, the Chicago Loop Alliance hosted Looptopia, a one-day festival of live music, dance and theater performances. (Organizers are planning for another event in 2008.)

While the rest of the world begins to rediscover Chicago, there are some for whom the city has always been “my kind of town.”

“I just love jogging along Lake Michigan, where my parents live,” says New York socialite Jamee Gregory (who gave up Chicago for Manhattan). “It goes for miles in both directions and is a great way to start the day.”

But take it from the native: Chicago winters are cold. “You need sunglasses and a wrap,” advises Gregory as a way to battle the wind.

And, in a fashionable bonus: “It’s the perfect city for fur.”

WHAT TO DOAs one resident put it, “If you are bored in Chicago for 15 minutes, you aren’t really trying.” The mercury takes a nosedive during the winter months, so Chicago has plenty of indoor attractions, namely the theater. The city boasts an impressive roster of storefront theater—where the likes of David Schwimmer, who founded Lookingglass Theatre Company, and Jeremy Piven, whose mother, Joyce, owns the Piven Theatre workshop in nearby Evanston—occasionally perform. Chicago is also home to the Steppenwolf Theater Company, which counts members like Joan Allen, John Malkovich and John Mahoney, and Second City, the famed improv club that launched the careers of comedians such as Stephen Colbert, Tina Fey, Amy Sedaris and Mike Meyers. And let’s not forget this is the city that gave us the Cusacks.

There’s also a great art scene, with no fewer than four major museums. The Chicago Art Institute is best known for its collection of French Impressionist and Postimpressionist paintings and also houses Grant Wood’s iconic American Gothic. A Jasper Johns exhibit will run until the beginning of next year.

The newly opened Chicago History Museum houses an assortment of city artifacts, including Abraham Lincoln’s deathbed, and in September, it will exhibit 50 couture pieces from its costume collection with labels such as Lanvin, Comme des Garçons, Chanel and Versace in the mix. The Museum of Contemporary Art is running an exhibit of rock ’n’ roll photography and art, titled “Sympathy for the Devil,” through January 6, and the Field Museum is best for those who get their kicks out of dinosaur bones. But Chicago art isn’t just about museums—the city also boasts a slew of galleries. Until December 29, Printworks Gallery will feature “Elegy for Isabella Blow,” a series of photographs and prints of the late British fashion editor, by artist and writer Audrey Niffengger, author of the best-selling The Time Traveler’s Wife.

The architectural boat tour on the Chicago River is a must, cruising by buildings constructed by Frank Lloyd Wright, Frank Gehry and Rem Koolhaas.

Once you’ve had your fill of culture, there’s always ice-skating at the rink in Millennium Park.

WHERE TO EAT & DRINKWhen Charlie Trotter opened his namesake restaurant in 1987, he paved the way for chefs such as Rick Tramonto and Gale Gand, owners of the haute eatery Tru, and Grant Achatz, partner at Alinea. All three acclaimed restaurants offer haute cuisine and extensive wine lists. Alinea is known for its over-the-top 20-course tasting menu.

That said, none of these establishments serve foie gras, as the city banned it from all menus last summer. So, for those in need of a fix, head to the Stained Glass in nearby Evanston (which can serve the delicacy since it’s located outside city limits). Another option is Chef’s Station, a shabby chic restaurant underneath the Davis Street El stop.

For less fancy affairs, foodie locals flock to Blackbird and its sister wine bar next door, Avec, for inventive dishes like gioia burrata salad with braised lobster mushrooms and haricots verts. Pane Caldo is a new Italian joint downtown and delacosta and Nacionale 27 are popular among the tapas crowd. Oprah’s chef, Art Smith, recently opened Table Fifty Two, where, despite his rep for keeping the talk-show host svelte, he serves up Southern comfort food such as buttermilk biscuits and fried chicken. (No wonder Winfrey’s prone to hitting up the more healthy Japonais, an upscale Japanese eatery.)

The best lunch for shoppers on the Miracle Mile is RL, the restaurant attached to Ralph Lauren’s flagship. The interior is full-on Ralph—all leather club chairs and dark wood—and the food, classics like cobb salad and burgers, is well executed.

For brunch, intrepid diners brave long wait lines at Cafe des Architectes in the Sofitel Hotel in River North, or head to the South Loop to Yolk, an eatery that, as its name suggests, specializes in traditional breakfast standbys such as scrambled eggs and french toast.

After dinner, Pops for Champagne, which just opened a new location in River North, is a favorite for its more than 100 varieties of bubbly and live jazz music. For afternoon tea, head to the Palm Court Lounge in the historic Drake Hotel, where scones and clotted cream are served daily.

WHERE TO STAYThe boutique hotel trend hasn’t caught on here yet (save for the James hotel, home to favorite steakhouse David Burke’s Prime), so the best places to stay are the gold-star standards on North Michigan Avenue. The Peninsula, the Four Seasons (where Oprah puts up her celebrity guests) and the Ritz-Carlton are all within blocks of each other and walking distance of Oak Street stores, River North restaurants and Lake Michigan. Locals agree the Peninsula is the poshest (Aniston reportedly checks in under the name “Mrs. Smith”) and concierge Todd Nelson has a black book of secret numbers to secure impossible-to-get tables at the city’s hot spots.

WHERE TO SHOPDowntown has all the department store standards (Neiman Marcus, Barneys New York and Saks Fifth Avenue), and designer boutiques are popping up with increasing frequency. Marc by Marc Jacobs is opening up in Bucktown, and Tory Burch, Jimmy Choo, Calypso, Scoop NYC and Intermix all have outposts on and around fashionable Oak Street. Material Possessions is the spot there for luxe home goods.

A 20-minute drive north, Lincoln Park could be considered Chicago’s version of New York’s SoHo. A few independent stores, such as high-end linen boutique Le Magasin and cosmetic and beauty emporium Endo Exo, are still standing in the charming neighborhood, but biggies like Cynthia Rowley and Kiehl’s are quickly moving in.

Instead, Bucktown is the new up-and-coming spot for retail, with Jacobs moving in next to existing shops Hegfinia and Helen Yi, which both sell a selection of young designers including Derek Lam and Alexander Wang. And to slip on under their clothes, locals stock up on underpinnings at nearby Raizy, where owner Renee Gertzfeld stocks an impressive selection of La Perla bras.

What’s most surprising about Chicago style is the number of fashion- forward boutiques that dot the city’s landscape. Ikram Goldman pioneered the movement when she opened her eponymous store. It’s where locals go for their fix of Alexander McQueen, Zac Posen and Miu Miu. Next door are Jake and Blake, unrelated shops that sell lines otherwise hard to find in these parts, such as See by Chloé, Steven Alan and Helmut Lang. (So popular among Second City shoppers, Jake has opened two other locations, one in Lakeview and one in the tony North Shore suburb of Winnetka.)

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